Put a hand up if you’ve ever…
🤚🏻Felt like everything is jacked.
🤚🏻Thought Substack is a space to make sense of it.
🤚🏻Felt like what you’re reading and watching in the news is not normal.
For today’s podcast I invited tribe member
(William A. for “Anonymous”; Finnegan is his nom de plume) from The Long Memo and Borderless Living to share his insights.Besides being an ad exceutive, father and writer, he used to be a political appointee under President Bush, known for his bluntness and experience in Republican politics. He has testified before Congress, briefed Presidents, and met with top officials—including foreign leaders and intelligence officers. Though he stayed out of the spotlight, he worked behind the scenes in high-security settings like the White House Situation Room, the Pentagon’s “Tank,” and ultra-sensitive Gang of Eight briefings.
We chatted for over 1.5 hours two weeks ago, and since then, Mr. Anonymous (as I like to call him) has been growing like crazy —already at 7,500 subscribers—even though he’s writing completely anonymously.
He’s not offering anything fancy (although he could) —no courses, no coaching, no book, no extras. Just a text-based newsletter and his insights. Which is why I needed to introduce you to this member of the Online Writing Club.
He also had a viral post on Notes with 3.000 likes and 875 restacks three days back
I told myself—I had to bring you this conversation today.
It fits perfectly with all the new things happening on Substack: the leaderboard (is it a good thing? a bad thing?), the new in-app payment option, graphs, and how About pages and tags are suddenly more important than ever.
So if you were one of the people who raised your hand when I asked how you're feeling about everything going on in the world—and about Substack still being this sacred little corner where we can make sense of it all and have fun, even though it's clearly going through some big changes…
This is what Mr. Anonymous had to say:
Let’s not sugarcoat it. Things are jacked.
*Warning ⚠️ Side effects of reading and listening may include sudden clarity on what migh be going on (I still want to be believe in Substack’s mission and vision), the urge to finally launch your Substack you've been overthinking for months and write with the end in mind.
This Podcast Interview is a Bombshell On Many Levels
I promise you—today's podcast episode will open your eyes on so many levels.
This isn’t one of those “same old, same old” interviews.
Nope. This one’s a bombshell. It sparks conversations. It challenges assumptions. It’ll make you stop, think, and maybe even re-think everything you thought you knew.
Because Mr. Anonymous shared that everything you’re watching, reading, and living through right now is not normal. And deep down, you know it too. You feel it in your gut. That creeping sense that something is off.
The world’s spinning, the headlines are breaking, and all the while, creators, dreamers, artists, solos—especially writers—are trying to carve out a space to make sense of it.
Substack is the latest promised land for writers. A place where people like you and me can own our audience, build a thriving, soulful, sustainable and healthy newsletter, and finally bypass and exit the noise of social media.
But here’s the harsh truth Mr. Anonymous shared with me:
Substack won’t stay like this forever.
🎙️If you say, “Kristina, let me listen to the show!”🎙️
Now you have the chance to listen to the interview or continue reading, if you prefer this.
You can listen to it as Substack podcast or on Spotify.
Enjoy the show!
If you’re listening via Spotify it would be awesome to get a review from you ⭐⭐⭐⭐⭐. You can really make a different with this small gesture. Thanks 🙏🏻
You can also watch our video interview:
To break it down for you, here are five core truths from Mr. Anonymous about what’s happening with Substack —right now—and what (new) writers can do about it:
1. Everything Is Jacked—And That’s Why You’re Here
I don’t even tell people who I am. My growth? It’s been purely because of the content. And the reason that content resonates? Because I make people feel like they’re not crazy.
You’re not crazy for feeling that this moment is not how it’s supposed to go. Something’s broken. And Substack—for now—is where people come to feel sane again. To find others who are quietly screaming the same things you are. That’s power. That’s community. That’s why you’re here.
But don’t mistake now for always.
2. Why Bestsellers Win (And Will Keep Winning)
If you’re already a bestseller on Substack, you’re probably going to be just fine.
You’ve already done the hard part:
You built an audience.
You kept them.
You turned them into paying subscribers.
And—hardest of all—you kept those people happy.
That is incredibly hard to do. That’s why Substack will favor the winners when the platform starts shifting. Because shift it will. As the ecosystem matures, Substack will need to pick winners and losers. That’s how the money works. That’s how the game works. And that’s what VC-backed platforms always do.
If you’re not a bestseller yet, your job is simple (but not easy):
Focus on your audience. Focus on value. Think like a publisher.
Reward people for giving you their time.
3. Substack Is Owned by Billionaires—Don’t Be Naïve
Let’s clear something up.
There’s this myth going around that Substack is this pure, indie haven for free expression. “The only thing not owned by billionaires,” they say.

You people jacked? Of course it’s owned by billionaires.
That’s not a conspiracy. That’s venture capital.
Venture capital is not altruistic. It’s not romantic. It’s not about vision. It’s about amplifying what already works, extracting maximum value, and exiting with a 20x return. That’s it.
So yes, Substack is currently friendly to writers. Yes, they let you keep your email list. That’s rare. That’s generous. That’s smart.
But let’s not pretend this platform isn’t following the same path as every other social media company:
Growth ➡️ consolidation ➡️ monetization ➡️ control.
They give us a beautiful field to grow our crops in. But eventually, they’ll decide who gets the water and the sun.
4. How Substack Will Go Down (and Signs to Watch For)
So how will it happen? Mr. Anonymous knows.
It starts with subtle changes. Alarming signs. Revenue squeezes. Algorithm tweaks. Pay-for-placement. Leaderboards tied to promotion. Boosting posts for visibility.
The red flags will be slow and quiet at first:
A 10% cut becomes 15%.
Data becomes the real currency.
Discovery gets gated behind pay-to-play.
Algorithm shifts to favor “premium partners.”
Political pressure from governments mounts.
You and I? We’re the “dumb fools” doing the hard part: writing content people actually want to read.
Substack gets a cut. But more importantly, they get the data. What we read. What we click. What we subscribe to. It’s a massive data-gathering machine—and it’s brilliant.
But it also means this:
At some point, when the stakes are high enough, the mission will bend to the money. The idealism will bow to the investors. And that’s when the platform you trusted starts to turn.
We’ve seen it happen before. Facebook. LinkedIn. Medium. YouTube. Nothing stays indie forever.
5. What Writers Can Do To Prepare (While It’s Still Early)
Here’s the good news: we’re still early.
Substack is right between the early innovation stage and the scale stage.
This is what I shared on Notes and
from Substack re-stacked and replied to it (before she left the company):There’s still time to build. Still time to grow a loyal audience. Still time to own your email list and your message.
But here’s the play:
Build trust. Build connection. Build value.
Don’t just aim for numbers and being part of the new leaderbord. Aim for bonding. Your ability to influence, grow, and earn will be tied to how deeply your readers trust you and what (value) you bring to their lives.
Want to future-proof your writing?
Diversify when you can.
Focus on what you help people feel.
Own your audience (email list first).
Stay awake. Watch for platform shifts.
Keep experimenting—formats, topics, tone.
And never assume a tool will stay what it is forever.
From Zero to Bestseller JUST With Writing
Online Writing Club tribe member Mr. Anonymous went from zero to bestseller only with his content.
I think this is a great sign that Substack’s build-in audience rewards the unique thoughts, ideas and topics we’re writing about. We don’t need to add aything fancy such as coaching sessions, coffee chats, access to a community, books, freebies etc. we can become a bestseller entirely on the basis of our WRITING and content - even if we use a pen name, want to stay anonymous and/or don’t want to go live, share a video or audio/podcast.
Substack is giving us tools. We can use them. Play with Notes. Try video. Go live. Add audio. Or only build our writing empire while the doors are still open.
All I want you to understand is: Don’t sleep on the reality that every creator platform has a cycle—and we’re almost halfway through it.
Smallstacker? The Window Is Open. It Won’t Be Open Forever. So Make Your Move Now.
You’re new, a smallstacker with only a handful subscribers, you have a book laucnh coming, want to sell or keep selling your book, are retired and want to earn some extra bucks, you need an accountability buddy, initial help and 365 days support on your way? Join our souldful membership experience and 350 writers struggling with the same things as you do.
🎉 A few days ago, we crossed 12,000 subscribers in the Online Writing Club. Twelve. Thousand. People. I'm honestly so grateful and excited that I wanted to give you something super special.
🎁 Get 40% OFF (Limited Time!) to Celebrate
To thank you and because I know how hard it is to start an email list and make money with your words, I’m offering 40% off access to the entire Online Writing Club experience.
✅ Get instant access to:
The Substack Notes Masterclass
The Recommendations Masterclass
Access to the whole library of Masterclasses
The full Substack School course
The full Medium School course
Private community access
All paid posts
BONUS:
The upcoming LIVE Masterclasses worh yours truly and powerhouse
from Medium and TEDx speaker, author and integrative physician .Building a Medium-Substack Flywheel with Dana
Finally Dare to Share Vulnerability in Your Writing with Dr. Tanmeet
The Podcasting Masterclass
The Substack LIVE Masterclass
BONUS: Become a Bestseller in 2025! (As we heard in the inteview, bestsellers will be winners. Let me help you!)
Resources (with discount): The Almost Daily Notes Writer, Get Started on Substack Notes, Notes Scheduler, Opened!, 1 Month Substck Content Planner, 12-Month Content Calendar…
Hands-on masterclasses with ALL amazing writers, creators, dreamers and artists I interview (+ access to all past events, replays). Maybe Mr. Anonymous will join us too!
👉 Click here to celebrate with me + claim your 40% off
Your Turn!
👉🏻Do you think Substack will stay writer-friendly forever?Have you ever seen a platform “turn” before? What did it feel like? What made you leave or stay?
🙏🏻🙏🏻Your feedback is just a spark but enough to keep me going so it would be wonderful to hear from you in the comments 🙏🏻🙏🏻
PS Tell us in the comments! This is a safe space. You can also meet us in the Chat.👈🏻
Speaking of naive... Mr. Anonymous lost credibility with me when he didn't know that The Rolling Stones were touring in 2024. Their Hackneyed Diamonds tour was also in conjunction with a newly released album by the same name.
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
"I don't want to ascribe malice where stupidity might be a better explanation" could apply to so many things today.
If you want to join our live with Finnegan tonight, here's how
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Hey Kristina, check this out, we've created the uprising!
Kornerz Social Network: Spontaneous video conversations, purpose-driven communities, and a token-based system empowering real leaders. https://kornerzsocialnetwork.substack.com
Kornerz.com
Thank you Kristina & Mr A for talking about this- it is so true and the truth hurts!
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Your last name is as bold as it gets. 😅
Hi Ivan, it's my real name :) It's British.
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
"what makes the boat go faster" . . . OK, what can we present as content that our readers will throw $$$ however what becomes of TRUTH, because in some cases TRUTH doesn't generate new subscribers. Now What?
For more,Bob: Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
I love this real talk too, I am taking notes 🙂 The value is how you make people feel. So so true!
Hey Gabby, see you later
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
So far . . . Proof that Substack is a freedom of expression space,
note that no airliner ever flown could have crashed in the manner alleged by the media on 9/11/2001 . . . and that is a TRUE STATEMENT.
What is the problem with bilionaires?
Hi Renato, Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Nothing. I wrote four pieces on them. :)
This is just brilliant. I will listening to this again and again.
Hi Bella, Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
I came to the same conclusion.. I need to listen to this again and again.. so many awesome bits to learn and understand.
Not uncommon for me to give people the fire hose. Happy to answer questions as they come up
Good read!
Hello Marcel, nice reading your wonderful feedback.
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
The Mr Anonymous podcast was a pleasant surprise.
He turned out to be a smart, articulate, connected, professional – with a good sense of humor.
He shares his insider’s view of the political, business, and advertising dynamics that are shaping the social media evolution.
He comments on his Substack experiences, both good and bad, and the multi-level issues we will face going forward.
He talks about the specific issues he is testing with his different publications and his legitimate concerns about social media's political and economic future.
Kristina maintained a fast, entertaining pace throughout the podcast, and managed to link the conversations to writers-club issues.
Thank you both.
Will you join us later? Would be lovely!
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
In the beginning, start-ups are so open to ideas. As the company grows and money starts flowing, the mind hardens, and values fade. They detach from the "why" behind their business. The business came to be because of a value they cherished and a problem they solved, which is all soon forgotten when greed sets in.
I loved the philosophical depth of your analysis.
Great job to you both.
Hello Amer, sorry for replying so late.
Maybe you're right that the mind of startup hardens over time as we can also see in our personal life.
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
What isn't? Billionaires end up owning everything in time.
If you'd like to discuss this, you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
The creator economy is genius for the big companies (like Meta & Google). Let people hustle to create media to keep attention for the advertisers. Before, that would cost a ton of money to make TV shows for the advertisers.
On the flip side, creator economy gives people a voice and a chance to create the media without going through networking and pitching to media companies.
So we still have a chance here before big media catches on.
We have a chance here. It'S a great platform to be on AND you can take your subscribers with you. You can't take your followers with you, Jeff.
For more: Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Of course this is all true. I’ve been thinking the exact same thing. Substack and Blue Sky are targets. What troubles me, “Finnegan” is that you don’t use your real name. And you worked for Bush? Come on, who are you?
I met him already but thanks!
Being a mere journalist, for me there’s an ethical problem with no ID. It also obscures crucial context. As you know, I like your stuff and it was interesting to hear your voice. Your pieces basically tell me what I already know but you have tons of energy (is it the single malt?) and you’re excellent at citing statistics and appear to have a working knowledge of economics so eminently quotable, assuming your numbers are right and that’s easily checked. A bit arrogant but respect for hitting proverbial nail on head more often than not. You worked for Bush, though? WTF? Inquiring minds…
Hi Susan, in case you'd like to meet Finnegan, here's a last minute invite: Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
And I hope you’ll share more “controversial” information. I’m a journalist and marketing is death to us - unfortunately necessary but still against my nature.
FWIW… Kristina and others I have contributed to know my identity. As for my own Substack… people judge the content alone. Was I POTUS? No. Was I a cabinet official. No. lol. But obviously I was someone in the room, saw the discussions, and can talk intelligently about the topics. That’s apparently what matters. If I were to write for you … you’d know my identity. I believe that level of transparency is necessary (as you do). But readers don’t care.
🤫 im just… an illusion. (Waves hands mysteriously) 😏
That said there is something liberating about it all. Reminds me of something Ray Teller (of Penn and Teller) taught me… about why he doesn’t talk in the act (because when they first started he used to) and what he said to me was… by not talking and interjecting his personality he forces the audience to have to engage in the illusions performance. It makes the whole thing more interesting and it forces the audience to figure it out.
Draw from that what you will.
What a refreshing podcast interview at the Online Writing Club about the 'politics' of wealth. This guy speaks truth about marketing strategies with rawness and realness.
"Substack is not the unicorn that breaks the cycle" of social media control - hmmm...
Kristina asks some really good questions - especially about the future of ads on Substack with a great answer from Mr. A.
"Now is the time to experiment on Substack!" How liberating to hear!
He mentioned a book called "Will It Make the Boat Go Faster?" by Ben Hunt-Davis to use with clients that I am gonna check out!
Hi Santou, will you join us?
Think it's 6pm London time: Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Another guy to pay attention to is a friend of mine… Dr Alan Bernard. He teaches about constraint theory and using it to understand how to bring about transformation. A final guy is Brian Moran called the 12 Week Year. I never met Brian but I did meet his wife… who essentially is his business director. I did some coaching with Brian’s org for awhile. 12 week year is about periodization of efforts. Very helpful.
Oh I need to check this out
This is fascinating. Day job haver here and I related to so much of this! Following you now.
Hi Dana, maybe you can join during lunch break ^^
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
I would but I can't figure out how to join!
Thanks
Loved listening to this interview!!
So refreshing to hear real talk. We are truly in the right place at the right time 🚀
Now just have to figure out what 'will make the boat go faster' 😅
Thank you both 🙏💕
Hi Janet, can you join later? Saw your DM, will reply!
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Thanks Kristina 🙏
I will be jumping ship once Ghost 6.0 is released.
If you'd like to talk more about Ghost vs. Substack, here's your chance, Michael:
You can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Hi Michael, Casey Newton left Substack for Ghost. One Medium writer and pub owner now is also using Ghost. Think it's an alternative but doesn't have a built-in audience. That's the cool thing about Substack. You have 5M paid subscriptions and most of these people are also using Notes as Substack is pushing the app.
So no matter what you're writing about readers are here just waiting for to discover your pub.
Think Ghost is nice if you want to "own" everything and create your own beautiful website etc.
All fair points Kristina but this is exactly the reason why I am specifically waiting for version 6 to be released and become available for those who prefer to self-host.
Version 6.0 introduces the ActivityPub integration which is specifically all about discovery and the potential reach is by orders of magnitude larger than what Substack has now or likely will EVER have.
https://activitypub.ghost.org/gone-surfing/
So you'd like to take your pub and move it to Ghost then? Once you know when it will be released tag me on Notes :) No form dates yet. Maybe I could feature Justin Cox who is using Ghost already and in one of our masterclasses highlighted the benefits. If discovery (as top of the funnel) will become better... this will change the game for sure. Thanks for bringing this to my attention. Speak soon!
I have looked at Ghost after they reached out to me.
I think, honestly, Substack provides many intangible benefits worth the extra cost. Most obvious being, if you move to something like Ghost, now the discovery of the content is considerably shifted back to the author, versus the platform.
For me... Substack is turnkey. I don't see a lot of reason to move yet.
My article, the podcast, etc., really has one message - stop deluding yourself into thinking the platform won't change.
The message was not "LEAVE! RUN! IT'S IMPLODING!" which is what effectively a lot of people seem to conclude.
Substack probably has about a year, maybe longer, realistically probably longer, until it starts to warp. I would imagine the 100M user mark is when things start to "get real," in terms of scale and money.
There are of course black swans... Trump Admin decides things like Substack are seditious... pow... party's over.
But assuming that doesn't happen... there is considerable runway to build an audience on Substack. I don't see that opportunity in Ghost. I'm not saying it won't become an opportunity... but right now? I don't see open source blah blah blah as advantageous to a turnkey system that is sucking in a massive audience daily, and plopping your ideas into an ecosystem that promotes discovery.
But what do I know? :D
My pleasure. Here is a recent interview with the ghost founder talking specifically about the ActivityPub integration which will unlock access to millions of users, including most people who are on threads as well as any other platform using that protocol like Mastodon, Pixelfed and PeerTube.
https://youtu.be/0vMkriMl-ic
Unfortunately, that seems to be the norm for platforms now. They start with good intensions and ideas, but then turn to the "dark side". The bigger they are, the worse it gets :(
Hu Julie, we're gonna talk about the dark side of Subsatck but of course also about all the good dtuff!
Here you can join our live with Finnegan today at 1pm EST
https://www.onlinewritingclub.com/p/substacks-secret-billionaire-backers?r=f1242&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Hi Julie! Nice reading from you here in the comments.
Sadly you're right — that does seem to be the pattern.
They start off with great intentions, serving creators, building community… and then once growth and investors come into play, things shift.
That’s actually one of the reasons I’ve been so drawn to Substack.
It still feels like it’s made for writers and readers first — not just shareholders. Hoping it stays that way :)
Kristina doesn't allow posting pics like I do at TLM... but if I could...
I think you know the one... "Aliens." :D